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Stereodivergent α-Allylation of Linear Aldehydes with Dual Iridium and Amine Catalysis

Simon Krautwald, Michael A. Schafroth, David Sarlah and Erick M. Carreira*

*Eidgenössische Technische Hochschule Zürich, 8093 Zürich, Switzerland, Email: carreiraorg.chem.ethz.ch

S. Krautwald, M. A. Schafroth, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc., 2014, 136, 3020-3023.

DOI: 10.1021/ja5003247 (free Supporting Information)



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Abstract

A fully stereodivergent, dual catalytic α-allylation of linear aldehydes proceeds via direct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter is crucial for achieving high enantio- and diastereoselectivity.

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Key Words

allylations


ID: J48-Y2014